{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,12,6]],"date-time":"2025-12-06T05:30:42Z","timestamp":1764999042739,"version":"3.46.0"},"reference-count":96,"publisher":"MDPI AG","issue":"4","license":[{"start":{"date-parts":[[2025,12,3]],"date-time":"2025-12-03T00:00:00Z","timestamp":1764720000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Brazilian Research Councils: Conselho Nacional do Desenvolvimento Cient\u00edfico e Tecnol\u00f3gico","award":["PQ-2022","308411\/2022-6","N\u00b0 32\/2023 P\u00f3s-Doutorado J\u00fanior\u2014PDJ 2023 174545\/2023-1"],"award-info":[{"award-number":["PQ-2022","308411\/2022-6","N\u00b0 32\/2023 P\u00f3s-Doutorado J\u00fanior\u2014PDJ 2023 174545\/2023-1"]}]},{"DOI":"10.13039\/501100002322","name":"Coordena\u00e7\u00e3o de Aperfei\u00e7oamento de Pessoal de N\u00edvel Superior","doi-asserted-by":"publisher","award":["CAPES-PROEX, 001"],"award-info":[{"award-number":["CAPES-PROEX, 001"]}],"id":[{"id":"10.13039\/501100002322","id-type":"DOI","asserted-by":"publisher"}]},{"name":"Funda\u00e7\u00e3o para a Ci\u00eancia e a Tecnologia","award":["UID\/PRR\/00313\/2025","UID\/00313\/2025"],"award-info":[{"award-number":["UID\/PRR\/00313\/2025","UID\/00313\/2025"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Future Pharmacology"],"abstract":"<jats:p>Background: Rapidly growing mycobacteria (RGM) are microorganisms with variable pathogenicity, which can cause different clinical forms of mycobacterioses. They can form structured communities at the liquid-air interface and adhere to animate and inanimate solid surfaces, characterizing one of their most powerful mechanisms of resistance and survival, named biofilms. Objectives: Here, a novel series of sulfamethoxazole (SMTZ) Schiff bases were obtained by the condensation of the primary amine from SMTZ core with six different aldehydes to evaluate their antimicrobial and antibiofilm activities, as well as physicochemical and in silico characteristics. Methods: The compounds L1\u2013L6 included: pyridoxal hydrochloride (L1), salicylaldehyde (L2), 3-methoxysalicylaldehyde (L3), 2-hydroxy-1-naphthaldehyde (L4), 3-allylsalicylaldehyde (L5), and 4-(diethylamino)salicylaldehyde (L6). MIC determination was performed against standard strains and seven clinical isolates. Time-kill assays, biofilm inhibition assays, atomic force microscopy, and peripheral blood mononuclear cell cytotoxicity assays were carried out. Density functional theory (DFT) calculations using quantum descriptors, Mulliken charges, Fukui functions, non-covalent interactions (NCI), and reduced density gradient (RDG), along with molecular docking calculations to DHS, LasR, and PqsR, supported the experimental trend. Results: The compounds L1\u2013L6 showed a significant capacity to inhibit the growth of RGM, with MIC values in the range of 0.61 to 1.22 \u03bcg mL\u22121, which are significantly lower than those observed for the parent compound SMTZ, demonstrating superior antimicrobial potency. To deepen antimicrobial activity assays, L1 was chosen for further evaluations and showed a significant ability to inhibit the growth of RGM in both planktonic and biofilm forms. In addition, atomic force microscopy views great changes in topography, electrical force, and nanomechanical properties of microorganisms. The cytotoxic assays with the peripheral blood mononuclear cell model suggest that the new compound may be considered as an antimicrobial alternative, as well as a safe substance showing selectivity indexes in the range of efficacy. Conclusions: Density functional theory (DFT) calculations were performed to obtain quantum descriptors, Mulliken charges, Fukui functions, non-covalent interactions (NCI), and reduced density gradient (RDG), which, with molecular docking calculations to DHS, LasR, and PqsR, supported the experimental trend.<\/jats:p>","DOI":"10.3390\/futurepharmacol5040072","type":"journal-article","created":{"date-parts":[[2025,12,5]],"date-time":"2025-12-05T17:35:17Z","timestamp":1764956117000},"page":"72","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Synthesis of New Schiff Bases Derived from Sulfamethoxazole and Aromatic Aldehydes with High Antibiofilm Activity in Rapidly Growing Mycobacteria Samples"],"prefix":"10.3390","volume":"5","author":[{"given":"Fallon dos Santos","family":"Siqueira","sequence":"first","affiliation":[{"name":"Mycobacteriology Laboratory, Graduate Program in Pharmaceutical Sciences, Department of Clinical and Toxicological Analysis, Federal University of Santa Maria, Santa Maria 97105-900, RS, Brazil"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2626-0375","authenticated-orcid":false,"given":"Josi\u00e9li Dem\u00e9trio","family":"Siqueira","sequence":"additional","affiliation":[{"name":"Inorganic Materials Laboratory, Department of Chemistry, Center for Natural and Exact Sciences (CCNE), Federal University of Santa Maria (UFSM), Santa Maria 97105-900, RS, Brazil"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2003-8420","authenticated-orcid":false,"given":"Alencar Kolinski","family":"Machado","sequence":"additional","affiliation":[{"name":"Graduate Program in Nanosciences, Franciscan University, Santa Maria 97010-032, RS, Brazil"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5659-159X","authenticated-orcid":false,"given":"Michele Rorato","family":"Sagrillo","sequence":"additional","affiliation":[{"name":"Graduate Program in Nanosciences, Franciscan University, Santa Maria 97010-032, RS, Brazil"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5956-2433","authenticated-orcid":false,"given":"Yuri Clemente Andrade","family":"Sokolovicz","sequence":"additional","affiliation":[{"name":"Inorganic Materials Laboratory, Department of Chemistry, Center for Natural and Exact Sciences (CCNE), Federal University of Santa Maria (UFSM), Santa Maria 97105-900, RS, Brazil"}]},{"given":"Marieli Friedrich","family":"Loreto","sequence":"additional","affiliation":[{"name":"Inorganic Materials Laboratory, Department of Chemistry, Center for Natural and Exact Sciences (CCNE), Federal University of Santa Maria (UFSM), Santa Maria 97105-900, RS, Brazil"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2521-3574","authenticated-orcid":false,"given":"Thiago Augusto","family":"de Lima Burgo","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Environmental Sciences, Institute of Biosciences, Letters and Exact Sciences, S\u00e3o Paulo State University, S\u00e3o Jos\u00e9 do Rio Preto 15054-000, SP, Brazil"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7004-0110","authenticated-orcid":false,"given":"Carlos","family":"Serpa","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Coimbra Chemistry Centre\u2014Institute of Molecular Science (CQC-IMS), University of Coimbra, Rua Larga s\/n, 3004-535 Coimbra, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6211-7659","authenticated-orcid":false,"given":"Ot\u00e1vio Augusto","family":"Chaves","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Coimbra Chemistry Centre\u2014Institute of Molecular Science (CQC-IMS), University of Coimbra, Rua Larga s\/n, 3004-535 Coimbra, Portugal"},{"name":"Laboratory of Immunopharmacology, Centro de Pesquisa, Inova\u00e7\u00e3o e Vigil\u00e2ncia em COVID-19 e Emerg\u00eancias Sanit\u00e1rias, Oswaldo Cruz Institute, Oswaldo Cruz Foundation, Rio de Janeiro 21040-361, RJ, Brazil"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9851-7793","authenticated-orcid":false,"given":"Matiko Anraku","family":"de Campos","sequence":"additional","affiliation":[{"name":"Mycobacteriology Laboratory, Graduate Program in Pharmaceutical Sciences, Department of Clinical and Toxicological Analysis, Federal University of Santa Maria, Santa Maria 97105-900, RS, Brazil"}]},{"given":"Davi Fernando","family":"Back","sequence":"additional","affiliation":[{"name":"Inorganic Materials Laboratory, Department of Chemistry, Center for Natural and Exact Sciences (CCNE), Federal University of Santa Maria (UFSM), Santa Maria 97105-900, RS, Brazil"}]}],"member":"1968","published-online":{"date-parts":[[2025,12,3]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"410","DOI":"10.1080\/08927014.2021.1925886","article-title":"Mycobacterial biofilms as players in human infections: A review","volume":"37","author":"Velazquez","year":"2021","journal-title":"Biofouling"},{"key":"ref_2","doi-asserted-by":"crossref","unstructured":"Varghese, B., Enani, E., Shoukri, M., AlThawadi, S., AlJohani, S., and Al-Hajoj, S. (2017). Emergence of rare species of nontuberculous mycobacteria as potential pathogens in Saudi Arabian clinical setting. PLoS Negl. Trop. Dis., 11.","DOI":"10.1371\/journal.pntd.0005288"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"324","DOI":"10.1016\/j.jinf.2015.12.007","article-title":"The antimicrobial susceptibility of non-tuberculous mycobacteria","volume":"72","author":"Cowman","year":"2016","journal-title":"J. Infect."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"51","DOI":"10.1080\/14787210.2018.1417036","article-title":"Biofilm-related disease","volume":"16","year":"2018","journal-title":"Expert Rev. Anti Infect. Ther."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"121","DOI":"10.1007\/978-3-642-28951-4_8","article-title":"Persister cells: Molecular mechanisms related to antibiotic tolerance","volume":"211","author":"Lewis","year":"2012","journal-title":"Handb. Exp. Pharmacol."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"555","DOI":"10.1038\/509555a","article-title":"Policy: An intergovernmental panel on antimicrobial resistance","volume":"509","author":"Woolhouse","year":"2014","journal-title":"Nature"},{"key":"ref_7","unstructured":"O\u2019Neill, J. (2016). Tackling Drug-Resistant Infections Globally: Final Report and Recommendation, Welcome Trust."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"5","DOI":"10.1007\/s11095-018-2535-x","article-title":"Pharmaceutical potential of a novel chitosan derivative Schiff base with special reference to antibacterial, anti-biofilm, antioxidant, anti-inflammatory, hemocompatibility and cytotoxic activities","volume":"36","author":"Ali","year":"2018","journal-title":"Pharm. Res."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"63","DOI":"10.1080\/13543776.2017.1252752","article-title":"Schiff bases in medicinal chemistry: A patent review (2010\u20132015)","volume":"27","author":"Hameed","year":"2017","journal-title":"Expert Opin. Ther. Pat."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1155\/2013\/362513","article-title":"Synthesis, characterization, and bioactivity of Schiff bases and their Cd2+, Zn2+, Cu2+ complexes derived from chloroacetophenone isomers with S-benzyldithiocarbazate and the X-ray crystal structure of S-benzyl-\u03b2-N-(4-chlorophenyl)methylenedithiocarbazate","volume":"2013","author":"Tahir","year":"2013","journal-title":"Bioinorg. Chem. Appl."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"2018","DOI":"10.2174\/1570180820666221031091246","article-title":"Synthetic Transformation of 4-Fluorobenzoic Acid to 4-Fluorobenzohydrazide Schiff Bases and 1,3,4-Oxadiazole Analogs Having DPPH Radical Scavenging Potential","volume":"20","author":"Khan","year":"2023","journal-title":"Lett. Drug Des. Discov."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"140136","DOI":"10.1016\/j.molstruc.2024.140136","article-title":"Exploring the Anti-Diabetic Activity of Benzimidazole Containing Schiff Base Derivatives: In Vitro \u03b1-Amylase, \u03b1-Glucosidase Inhibitions and In Silico Studies","volume":"1321","author":"Shakoor","year":"2025","journal-title":"J. Mol. Struct."},{"key":"ref_13","doi-asserted-by":"crossref","unstructured":"Shakoor, A., Jan, F., Rahman, S., Ali, M., Ibrahim, M., Khan, H., and Khan, M. (2025). Synthesis, Urease Inhibitory Activity, Molecular Docking, Dynamics, MMGBSA and DFT Studies of Hydrazone-Schiff Bases Bearing Benzimidazole Scaffold. Chem. Biodivers., 22.","DOI":"10.1002\/cbdv.202402096"},{"key":"ref_14","first-page":"e7768","article-title":"Synthesis, structural determination, DFT calculation and biological evaluation supported by molecular docking approach of some new complexes incorporating (E)-N\u2019-(3,5-di-tert-butyl-2-hydroxybenzylidene) isonicotino hydrazide ligand","volume":"39","author":"Qasem","year":"2024","journal-title":"Appl. Organomet. Chem."},{"key":"ref_15","doi-asserted-by":"crossref","unstructured":"Anwer, K.E., Hamza, Z.K., and Ramadan, R.M. (2023). Synthesis, spectroscopic, DFT calculations, biological activity, SAR, and molecular docking studies of novel bioactive pyridine derivatives. Sci. Rep., 13.","DOI":"10.1038\/s41598-023-42714-w"},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"4784","DOI":"10.1080\/10406638.2023.2257843","article-title":"Synthesis, biological evaluation, DFT calculations and molecular docking of 5-arylidene-thiazolidine-2,4-dione derivatives","volume":"44","author":"Zine","year":"2023","journal-title":"Polycycl. Aromat. Compd."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"100146","DOI":"10.1016\/j.chphi.2022.100146","article-title":"Molecular modeling, DFT studies and biological evaluation of methyl 2,8-dichloro-1,2-dihydroquinoline-3-carboxylate. Chem","volume":"6","author":"Agwupuye","year":"2023","journal-title":"Phys. Impact"},{"key":"ref_18","doi-asserted-by":"crossref","unstructured":"Rahman, J., Tareq, A.M., Hossain, M.M., Sakib, S.A., Islam, M.N., Ali, M.H., Uddin, A.B.M.N., Hoque, M., Nasrin, M.S., and Emran, T.B. (2020). Biological evaluation, DFT calculations and molecular docking studies on the antidepressant and cytotoxicity activities of Cycas pectinata Buch.-Ham. compounds. Pharmaceuticals, 13.","DOI":"10.3390\/ph13090232"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"138815","DOI":"10.1016\/j.molstruc.2024.138815","article-title":"Synthesis, structural characterization, Fukui functions, DFT calculations, molecular docking and biological efficiency of some novel heterocyclic systems","volume":"1314","author":"Ibrahim","year":"2024","journal-title":"J. Mol. Struct."},{"key":"ref_20","doi-asserted-by":"crossref","unstructured":"Carre\u00f1o, A., P\u00e1ez-Hern\u00e1ndez, D., Cantero-L\u00f3pez, P., Z\u00fa\u00f1iga, C., Nevermann, J., Ram\u00edrez-Osorio, A., Gacit\u00faa, M., Oyarz\u00fan, P., S\u00e1ez-Cortez, F., and Polanco, R. (2020). Structural characterization, DFT calculation, NCI, scan-rate analysis and antifungal activity against Botrytis cinerea of (E)-2-{[(2-aminopyridin-2-yl)imino]-methyl}-4,6-di-tert-butylphenol (pyridine Schiff base). Molecules, 25.","DOI":"10.3390\/molecules25122741"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"112","DOI":"10.1107\/S0108767307043930","article-title":"A short history of SHELX","volume":"64","author":"Sheldrick","year":"2008","journal-title":"Acta Crystallogr. A"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053229614024218","article-title":"Crystal structure refinement with SHELXL","volume":"71","author":"Sheldrick","year":"2015","journal-title":"Acta Crystallogr. C"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"565","DOI":"10.1107\/S0021889897003117","article-title":"ORTEP-3 for Windows\u2014A version of ORTEP-III with a graphical user interface (GUI)","volume":"30","author":"Farrugia","year":"1997","journal-title":"J. Appl. Crystallogr."},{"key":"ref_24","unstructured":"Putz, H., and Barndenburg, K. (1995). Diamond\u2014Crystal and Molecular Structure Visualization, Crystal Impact."},{"key":"ref_25","unstructured":"CLSI (2015). Susceptibility Testing of Mycobacteria, Nocardia spp. and Other Aerobic Actinomycetes, Clinical and Laboratory Standards Institute (CLSI). [3rd ed.]."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"893","DOI":"10.1080\/08927014.2018.1514497","article-title":"Sulfamethoxazole derivatives complexed with metals: A new alternative against biofilms of rapidly growing mycobacteria","volume":"34","author":"Siqueira","year":"2018","journal-title":"Biofouling"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"45","DOI":"10.1016\/j.tube.2019.06.001","article-title":"Preliminary evaluation of the positively and negatively charge effects of tetra-substituted porphyrins on photoinactivation of rapidly growing mycobacteria","volume":"117","author":"Guterres","year":"2019","journal-title":"Tuberculosis"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"144","DOI":"10.1016\/j.micpath.2020.104455","article-title":"Peripheral tetra-cationic Pt(II) porphyrins photo-inactivating rapidly growing mycobacteria: First application in mycobacteriology","volume":"148","author":"Rossi","year":"2020","journal-title":"Microb. Pathog."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"229","DOI":"10.1016\/j.micpath.2016.08.017","article-title":"Antibiofilm effect of antimicrobials used in the therapy of mycobacteriosis","volume":"99","author":"Flores","year":"2016","journal-title":"Microb. Pathog."},{"key":"ref_30","unstructured":"Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Petersson, G.A., and Nakatsuji, H. (2016). Gaussian 09, Revision C.01., Gaussian, Inc."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"1429","DOI":"10.1002\/jcc.23266","article-title":"NBO 6.0: Natural Bond Orbital Analysis Program","volume":"34","author":"Glendening","year":"2013","journal-title":"J. Comput. Chem."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"580","DOI":"10.1002\/jcc.22885","article-title":"Multiwfn: A multifunctional wavefunction analyzer","volume":"33","author":"Lu","year":"2012","journal-title":"J. Comput. Chem."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"082503","DOI":"10.1063\/5.0216272","article-title":"A comprehensive electron wavefunction analysis toolbox for chemists, Multiwfn","volume":"161","author":"Lu","year":"2024","journal-title":"J. Chem. Phys."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"2492","DOI":"10.1007\/s00894-014-2492-1","article-title":"Introducing UCA-FUKUI software: Reactivity-index calculations","volume":"20","author":"Zorrilla","year":"2014","journal-title":"J. Mol. Model."},{"key":"ref_35","unstructured":"(2025, July 01). Chemcraft\u2014Graphical Software for Visualization of Quantum Chemistry Computations, Version 1.8, Build 682. Available online: https:\/\/www.chemcraftprog.com\/."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"4049","DOI":"10.1021\/ja00326a036","article-title":"Density functional approach to the frontier-electron theory of chemical reactivity","volume":"106","author":"Parr","year":"1984","journal-title":"J. Am. Chem. Soc."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"6723","DOI":"10.1073\/pnas.82.20.6723","article-title":"Hardness, softness, and the Fukui function in the electronic theory of metals and catalysis","volume":"82","author":"Yang","year":"1985","journal-title":"Proc. Natl. Acad. Sci. USA"},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"6498","DOI":"10.1021\/ja100936w","article-title":"Revealing noncovalent interactions","volume":"132","author":"Johnson","year":"2010","journal-title":"J. Am. Chem. Soc."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"12983","DOI":"10.1021\/jp204278k","article-title":"Analysis of hydrogen-bond interaction potentials from the electron density: Integration of noncovalent interaction regions","volume":"115","author":"Yang","year":"2011","journal-title":"J. Phys. Chem. A"},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"1705","DOI":"10.1016\/j.str.2004.07.011","article-title":"Crystal Structure of 7,8-Dihydropteroate Synthase from Bacillus anthracis","volume":"12","author":"Babaoglu","year":"2004","journal-title":"Structure"},{"key":"ref_41","doi-asserted-by":"crossref","unstructured":"Ilangovan, A., Fletcher, M., Rampioni, G., Pustelny, C., Rumbaugh, K., Heeb, S., C\u00e1mara, M., Truman, A., Chhabra, S.R., and Emsley, J. (2013). Structural Basis for Native Agonist and Synthetic Inhibitor Recognition by the Pseudomonas aeruginosa Quorum Sensing Regulator PqsR (MvfR). PLoS Pathog., 9.","DOI":"10.1371\/journal.ppat.1003508"},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"105960","DOI":"10.1016\/j.micpath.2022.105960","article-title":"Antibacterial, antifungal, and anti-biofilm effects of sulfamethoxazole-complexes against pulmonary infection agents","volume":"175","author":"Siqueira","year":"2023","journal-title":"Microb. Pathog."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"W530","DOI":"10.1093\/nar\/gkab294","article-title":"PLIP 2021: Expanding the scope of the protein-ligand interaction profiler to DNA and RNA","volume":"49","author":"Adasme","year":"2021","journal-title":"Nucleic Acids Res."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"35","DOI":"10.1016\/0166-1280(89)85148-6","article-title":"On the vibrational transition selection rules for the centrosymmetric hydrogen-bonded dimeric systems","volume":"187","author":"Flakus","year":"1989","journal-title":"J. Mol. Struct. Theochem"},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"97","DOI":"10.1016\/S0022-2860(98)00318-4","article-title":"\u2018Long-range\u2019 isotopic H\/D effects in the infrared spectra of the centrosymmetric dimeric systems of hydrogen bonds","volume":"447","author":"Flakus","year":"1998","journal-title":"J. Mol. Struct."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"2486","DOI":"10.1021\/ja9800277","article-title":"Self-assembled monolayers stabilized by three-dimensional networks of hydrogen bonds","volume":"120","author":"Clegg","year":"1998","journal-title":"J. Am. Chem. Soc."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"1831","DOI":"10.1021\/jo901503d","article-title":"Enzyme catalysis by hydrogen bonds: The balance between transition state binding and substrate binding in oxyanion holes","volume":"75","author":"Goodman","year":"2010","journal-title":"J. Org. Chem."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"275","DOI":"10.1002\/(SICI)1097-0134(19990515)35:3<275::AID-PROT1>3.0.CO;2-V","article-title":"High-precision measurement of hydrogen bond lengths in proteins by nuclear magnetic resonance methods. Proteins Struct","volume":"35","author":"Harris","year":"1999","journal-title":"Funct. Bioinf."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"31","DOI":"10.1007\/s41745-019-00141-9","article-title":"Strong and weak hydrogen bonds in protein\u2013ligand recognition","volume":"100","author":"Bulusu","year":"2020","journal-title":"J. Indian Inst. Sci."},{"key":"ref_50","first-page":"e202406024","article-title":"Strengthening an intramolecular non-classical hydrogen bond to get in shape for binding","volume":"63","author":"Varga","year":"2024","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"468","DOI":"10.1016\/j.ijbiomac.2008.09.004","article-title":"Non-classical hydrogen bonds in interleukins: The role of C\u2013H\u22efO interactions","volume":"43","author":"Anand","year":"2008","journal-title":"Int. J. Biol. Macromol."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"217","DOI":"10.1140\/epjd\/e2005-00317-0","article-title":"Hydrogen bonds: Relation between lengths and electron densities at bond critical points","volume":"37","author":"Tang","year":"2006","journal-title":"Eur. Phys. J. D"},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"1381","DOI":"10.1039\/c2sc00764a","article-title":"Hydrogen bonds with fluorine, studies in solution, in gas phase and by computations, conflicting conclusions from crystallographic analyses","volume":"3","author":"Schneider","year":"2012","journal-title":"Chem. Sci."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"1637","DOI":"10.1351\/PAC-REC-10-01-02","article-title":"Definition of the hydrogen bond (IUPAC Recommendations 2011)","volume":"83","author":"Arunan","year":"2011","journal-title":"Pure Appl. Chem."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"17482","DOI":"10.1039\/D0CP01508C","article-title":"C\u2013H\u22efS Interaction exhibits all the characteristics of conventional hydrogen bonds","volume":"22","author":"Ghosh","year":"2020","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"173","DOI":"10.1016\/j.jorganchem.2016.08.023","article-title":"Organometallic complexes of Schiff bases: Recent progress in oxidation catalysis","volume":"822","author":"Zoubi","year":"2016","journal-title":"J. Organomet. Chem."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"563","DOI":"10.1038\/nrmicro.2016.94","article-title":"Biofilms: An emergent form of bacterial life","volume":"14","author":"Flemming","year":"2016","journal-title":"Nat. Rev. Microbiol."},{"key":"ref_58","first-page":"5040","article-title":"Synthesis, characterization of Schiff base metal complexes and their biological investigation","volume":"33","author":"Mahmoud","year":"2019","journal-title":"Appl. Organomet. Chem."},{"key":"ref_59","doi-asserted-by":"crossref","unstructured":"Siqueira, J.D., de Pellegrin, S.F., dos Santos, S.S., Iglesias, B.A., Piquini, P.C., Arantes, L.P., Soares, F.A., Chaves, O.A., Neves, A., and Back, D.F. (2020). SOD activity of new copper(II) complexes with ligands derived from pyridoxal and toxicity in Caenorhabditis elegans. J. Inorg. Biochem., 204.","DOI":"10.1016\/j.jinorgbio.2019.110950"},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"678","DOI":"10.1016\/j.saa.2005.12.029","article-title":"Synthesis, characterization, electrochemistry, catalytic and biological activities of ruthenium(III) complexes with bidentate N,O\/S donor ligands","volume":"65","author":"Balasubramanian","year":"2006","journal-title":"Spectrochim. Acta A"},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"4176","DOI":"10.1021\/acs.cgd.0c00466","article-title":"Chiral oxazolidine complexes derived from phenolic Schiff bases","volume":"20","author":"Mayans","year":"2020","journal-title":"Cryst. Growth Des."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"49","DOI":"10.1002\/aoc.4903","article-title":"Peroxidase activity of new mixed-valence cobalt complexes with ligands derived from pyridoxal","volume":"33","author":"Fontana","year":"2019","journal-title":"Appl. Organomet. Chem."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"110","DOI":"10.1016\/j.jinorgbio.2019.110800","article-title":"In vitro tyrosinase, acetylcholinesterase, and HSA evaluation of dioxidovanadium (V) complexes: An experimental and theoretical approach","volume":"200","author":"Chaves","year":"2019","journal-title":"J. Inorg. Biochem."},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"1673","DOI":"10.1002\/adsc.201701475","article-title":"Copper(II)-Schiff base complex-functionalized polyacrylonitrile fiber as a green efficient heterogeneous catalyst for one-pot multicomponent syntheses of 1,2,3-triazoles and propargylamines","volume":"360","author":"Li","year":"2018","journal-title":"Adv. Synth. Catal."},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"268","DOI":"10.1111\/j.1469-0691.2011.03570.x","article-title":"Multidrug-resistant, extensively drug-resistant and pandrug-resistant bacteria: An international expert proposal for interim standard definition for acquired resistance","volume":"18","author":"Magiorakos","year":"2012","journal-title":"Clin. Microbiol. Infect."},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"149","DOI":"10.1016\/j.drup.2012.04.001","article-title":"Resistance mechanisms and drug susceptibility testing of nontuberculous mycobacteria","volume":"15","author":"Boeree","year":"2012","journal-title":"Drug Resist. Updat."},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"3036","DOI":"10.1016\/j.ccr.2012.07.001","article-title":"Coordination chemistry of vitamin B6 and derivatives: A structural overview","volume":"256","author":"Casas","year":"2012","journal-title":"Coord. Chem. Rev."},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"150","DOI":"10.1016\/j.ica.2014.11.033","article-title":"Formation of an unusual pyridoxal derivative: Characterization of Cu(II), Ni(II) and Zn(II) complexes and evaluation of binding to DNA and to human serum albumin","volume":"426","author":"Mukherjee","year":"2015","journal-title":"Inorg. Chim. Acta"},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"732","DOI":"10.1002\/ejic.200400481","article-title":"Vanadium (IV and V) complexes of Schiff bases and reduced Schiff bases derived from the reaction of aromatic o-hydroxyaldehydes and diamines: Synthesis, characterisation and solution studies","volume":"4","author":"Correia","year":"2005","journal-title":"Eur. J. Inorg. Chem."},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"7557","DOI":"10.1128\/AAC.02995-14","article-title":"Intra- and extracellular activities of trimethoprim-sulfamethoxazole against susceptible and multidrug-resistant Mycobacterium tuberculosis","volume":"58","author":"Davies","year":"2014","journal-title":"Antimicrob. Agents Chemother."},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"96","DOI":"10.1016\/j.saa.2014.03.019","article-title":"Synthesis, characterization, and antibacterial activity of a Schiff base derived from cephalexin and sulphathiazole and its transition metal complexes","volume":"129","author":"Anacona","year":"2014","journal-title":"Spectrochim. Acta A"},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"e01521","DOI":"10.1016\/j.heliyon.2019.e01521","article-title":"Sulfamerazine Schiff-base complex intercalated layered double hydroxide: Synthesis, characterization, and antimicrobial activity","volume":"5","author":"Barnabas","year":"2019","journal-title":"Heliyon"},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"1573","DOI":"10.3390\/molecules22091573","article-title":"Sulfadiazine salicylaldehyde-based Schiff bases: Synthesis, antimicrobial activity and cytotoxicity","volume":"22","year":"2017","journal-title":"Molecules"},{"key":"ref_74","first-page":"103","article-title":"Synthesis and antibacterial activity of the sulfonamide-based Schiff base and its transition metal (II) complexes","volume":"31","author":"Khan","year":"2018","journal-title":"Pak. J. Pharm. Sci."},{"key":"ref_75","doi-asserted-by":"crossref","first-page":"1189","DOI":"10.1080\/08927014.2013.832223","article-title":"Diverse plant extracts and trans-resveratrol inhibit biofilm formation and swarming of Escherichia coli O157:H7","volume":"29","author":"Lee","year":"2013","journal-title":"Biofouling"},{"key":"ref_76","doi-asserted-by":"crossref","first-page":"1318","DOI":"10.1126\/science.284.5418.1318","article-title":"Bacterial biofilms: A common cause of persistent infections","volume":"284","author":"Costerton","year":"1999","journal-title":"Science"},{"key":"ref_77","doi-asserted-by":"crossref","first-page":"6","DOI":"10.1016\/j.micpath.2017.08.008","article-title":"Anti-biofilm activity of A22 ((S-3,4-dichlorobenzyl) isothiourea hydrochloride) against Pseudomonas aeruginosa: Influence on biofilm formation, motility and bioadhesion","volume":"111","author":"Bonez","year":"2017","journal-title":"Microb. Pathog."},{"key":"ref_78","doi-asserted-by":"crossref","unstructured":"Maunders, E., and Welch, M. (2017). Matrix exopolysaccharides: The sticky side of biofilm formation. FEMS Microbiol. Lett., 364.","DOI":"10.1093\/femsle\/fnx120"},{"key":"ref_79","doi-asserted-by":"crossref","unstructured":"Mu\u00f1oz-Egea, M.C., Akir, A., and Esteban, J. (2023). Mycobacterium biofilms. Biofilm, 5.","DOI":"10.1016\/j.bioflm.2023.100107"},{"key":"ref_80","doi-asserted-by":"crossref","first-page":"184","DOI":"10.1186\/1471-2180-8-184","article-title":"Biofilm development by potentially pathogenic non-pigmented rapidly growing mycobacteria","volume":"8","author":"Esteban","year":"2008","journal-title":"BMC Microbiol."},{"key":"ref_81","unstructured":"Brazil National Health Surveillance Agency (2009). Joint Technical Note No. 01\/2009\u2014SVS\/MS and ANVISA, Infections Caused by Rapidly Growing Mycobacteria: Flow of Notifications, Clinical and Microbiological Diagnoses and Treatment, Brazil National Health Surveillance Agency."},{"key":"ref_82","first-page":"91","article-title":"Metal complexes derived from Schiff bases and semicarbazones for biomedical and allied applications: A review","volume":"14","author":"More","year":"2019","journal-title":"Mater. Today Chem."},{"key":"ref_83","doi-asserted-by":"crossref","first-page":"497","DOI":"10.1016\/j.micpath.2017.07.040","article-title":"Antibiofilm potential of synthetic 2-amino-5-chlorobenzophenone Schiff bases and its confirmation through fluorescence microscopy","volume":"110","author":"Arshia","year":"2017","journal-title":"Microb. Pathog."},{"key":"ref_84","first-page":"113","article-title":"Biofilmes bacterianos patog\u00eanicos: Aspectos gerais, import\u00e2ncia cl\u00ednica e estrat\u00e9gias de combate","volume":"14","author":"Trentin","year":"2013","journal-title":"Rev. Liberato"},{"key":"ref_85","first-page":"210","article-title":"Nontuberculous mycobacterial pulmonary infections","volume":"6","author":"Johnson","year":"2014","journal-title":"J. Thorac. Dis."},{"key":"ref_86","doi-asserted-by":"crossref","first-page":"285","DOI":"10.1186\/s13075-017-1490-y","article-title":"Efficacy, safety, and tolerability of secukinumab in patients with active ankylosing spondylitis: A randomized, double-blind phase 3 study, MEASURE 3","volume":"19","author":"Pavelka","year":"2017","journal-title":"Arthritis Res. Ther."},{"key":"ref_87","doi-asserted-by":"crossref","first-page":"e1343","DOI":"10.1038\/cddis.2014.313","article-title":"Bim is a crucial regulator of apoptosis induced by Mycobacterium tuberculosis","volume":"5","author":"Aguilo","year":"2014","journal-title":"Cell Death Dis."},{"key":"ref_88","doi-asserted-by":"crossref","first-page":"1227","DOI":"10.2147\/IJN.S121956","article-title":"The antimicrobial activity of nanoparticles: Present situation and prospects for the future","volume":"12","author":"Wang","year":"2017","journal-title":"Int. J. Nanomedicine"},{"key":"ref_89","doi-asserted-by":"crossref","unstructured":"Martins, F.M., Sokolovicz, Y.C.A., Oliveira, M.M., Serpa, C., Chaves, O.A., and Back, D.F. (2025). Synthesis, structural characterization, and in silico antiviral prediction of novel DyIII-, YIII-, and EuIII-pyridoxal helicates. Inorganics, 13.","DOI":"10.3390\/inorganics13080252"},{"key":"ref_90","doi-asserted-by":"crossref","first-page":"e29566","DOI":"10.1016\/j.heliyon.2024.e29566","article-title":"Spectroscopic characterization, DFT, antimicrobial activity and molecular docking studies on 4,5-bis[(E)-2-phenylethenyl]-1H,1\u2032H-2,2\u2032-biimidazole","volume":"10","author":"Kiruthika","year":"2024","journal-title":"Heliyon"},{"key":"ref_91","doi-asserted-by":"crossref","first-page":"123568","DOI":"10.1016\/j.saa.2023.123568","article-title":"Structural activity, spectroscopic, Fukui, NCI, AIM, IGM combined with molecular docking and molecular dynamics simulation on 4-methylpyridinium 4-hydroxybenzoate-potent drug anti-leukemia cancer","volume":"306","author":"Divya","year":"2024","journal-title":"Spectrochim. Acta A"},{"key":"ref_92","doi-asserted-by":"crossref","first-page":"2529","DOI":"10.1039\/C4CS00343H","article-title":"Ruthenium complexes as antimicrobial agents","volume":"44","author":"Li","year":"2015","journal-title":"Chem. Soc. Rev."},{"key":"ref_93","doi-asserted-by":"crossref","first-page":"555","DOI":"10.1080\/08927014.2021.1939019","article-title":"Molecular docking, quorum quenching effect, antibiofilm activity and safety profile of silver-complexed sulfonamide on Pseudomonas aeruginosa","volume":"37","author":"Siqueira","year":"2021","journal-title":"Biofouling"},{"key":"ref_94","doi-asserted-by":"crossref","first-page":"84","DOI":"10.1016\/j.micron.2018.05.005","article-title":"Effect of ampicillin on adhesive properties of bacteria examined by atomic force microscopy","volume":"112","author":"Laskowski","year":"2018","journal-title":"Micron"},{"key":"ref_95","doi-asserted-by":"crossref","first-page":"20150293","DOI":"10.1098\/rspb.2015.0293","article-title":"Insect antimicrobial peptides show potentiating functional interactions against Gram-negative bacteria","volume":"282","author":"Rahnamaeian","year":"2015","journal-title":"Proc. R. Soc. B"},{"key":"ref_96","doi-asserted-by":"crossref","first-page":"269","DOI":"10.1007\/s10534-020-00251-3","article-title":"Metal center ion effects on photoinactivating rapidly growing mycobacteria using water-soluble tetra-cationic porphyrins","volume":"33","author":"Guterres","year":"2020","journal-title":"BioMetals"}],"container-title":["Future Pharmacology"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/2673-9879\/5\/4\/72\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,12,6]],"date-time":"2025-12-06T05:24:56Z","timestamp":1764998696000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/2673-9879\/5\/4\/72"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,12,3]]},"references-count":96,"journal-issue":{"issue":"4","published-online":{"date-parts":[[2025,12]]}},"alternative-id":["futurepharmacol5040072"],"URL":"https:\/\/doi.org\/10.3390\/futurepharmacol5040072","relation":{},"ISSN":["2673-9879"],"issn-type":[{"type":"electronic","value":"2673-9879"}],"subject":[],"published":{"date-parts":[[2025,12,3]]}}}